Syntheses of New Amino and Aziridino Sugar Derivatives of Potential Biochemical Interest

Abstract

AbstractEfficient one‐pot syntheses of some amino and aziridino sugars of potential biochemical interest are developed by way of a CN coupling reaction between suitably protected sugars and esters of p‐aminobenzoic acid. The free amino function of the latter are utilized to cause SN2 displacement of the triflyl group in the sugar triflates 1–3 providing a new class of amino sugars (4–8). The reactions of 4 and 5 with Et2OBF3 in trimethylsilyl azide afford a new type of aziridino sugars (9–10) through a novel isomerization of an α‐iminooxirane into an α‐hydroxyepimine. The reaction pathway also provides benzyl 4‐[4‐(tert‐butyloxycarbonyl)phenylamino]‐4‐deoxy‐β‐L‐lyxopyranoside (11) and its α‐D‐isomer 12. The conformation of compounds 4–11 are supported by 1H‐ and 13C‐NMR spectroscopy.